(3R,4S)-3-Allyl-4-(4-methoxy-phenyl)-2-oxo-6-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine-3-carboxylic acid methyl ester | 138663-30-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: (3R,4S)-3-Allyl-4-(4-methoxy-phenyl)-2-oxo-6-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine-3-carboxylic acid methyl ester
• 英文别名: methyl (3R,4S)-4-(4-methoxyphenyl)-2-oxo-3-prop-2-enyl-6-(trifluoromethyl)-4,5-dihydro-1H-1-benzazepine-3-carboxylate
• CAS: 138663-30-6
• 化学式: C₂₃H₂₂F₃NO₄
• 分子量: 433.427
• InChiKey: ACFAPWVBWLYQIC-PGRDOPGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  31
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  64.6
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (3R,4S)-3-Allyl-4-(4-methoxy-phenyl)-2-oxo-6-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine-3-carboxylic acid methyl ester 在 对氨基苯酚 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成 (R)-3-Allyl-4-(4-methoxy-phenyl)-6-trifluoromethyl-1,3,4,5-tetrahydro-benzo[b]azepin-2-one
  参考文献：
  名称：

  Benzazepinone calcium channel blockers. 3. Synthesis and structure-activity studies of 3-alkylbenzazepinones

  摘要：

  As part of a program aimed at identifying novel analogues of diltiazem, we developed several synthetic routes for 3-alkylbenzazepinones, both in racemic and nonracemic form. Structure-activity relationship studies in this series have led to identification of several analogues as potent calcium channel blocking agents, both in vitro and in vivo. Analogues containing a 6-trifluoromethyl substituent (17a and 17b) are the most potent vasorelaxants in vitro. The oral antihypertensive activity of these compounds is comparable to its 3-acetoxy derivative 1 (X = 6-CF3) and 8-chlorodiltiazem (2b). The 3-allyl analogue 17c is a more potent antihypertensive agent than 17a, 17b, or 8-chlorodiltiazem (2b), and has a longer duration of action in vivo.

  DOI：

  10.1021/jm00082a019
• 作为产物：
  描述：

  (3R,4S)-3-Allyl-1-methoxymethyl-4-(4-methoxy-phenyl)-2-oxo-6-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine-3-carboxylic acid methyl ester 在 硫酸 、 lithium bromide 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以83%的产率得到(3R,4S)-3-Allyl-4-(4-methoxy-phenyl)-2-oxo-6-trifluoromethyl-2,3,4,5-tetrahydro-1H-benzo[b]azepine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Benzazepinone calcium channel blockers. 3. Synthesis and structure-activity studies of 3-alkylbenzazepinones

  摘要：

  As part of a program aimed at identifying novel analogues of diltiazem, we developed several synthetic routes for 3-alkylbenzazepinones, both in racemic and nonracemic form. Structure-activity relationship studies in this series have led to identification of several analogues as potent calcium channel blocking agents, both in vitro and in vivo. Analogues containing a 6-trifluoromethyl substituent (17a and 17b) are the most potent vasorelaxants in vitro. The oral antihypertensive activity of these compounds is comparable to its 3-acetoxy derivative 1 (X = 6-CF3) and 8-chlorodiltiazem (2b). The 3-allyl analogue 17c is a more potent antihypertensive agent than 17a, 17b, or 8-chlorodiltiazem (2b), and has a longer duration of action in vivo.

  DOI：

  10.1021/jm00082a019